Boron tribromide → Vatalanib metabolite M26

HRID 1384150Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1384150
B(Br)(Br)Br.[Cl:5][C:6]1[CH:29]=[CH:28][C:9]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([CH2:21][C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)=[N:13][N:12]=2)=[CH:8][C:7]=1[O:30]C>ClCCl>[Cl:5][C:6]1[CH:29]=[CH:28][C:9]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([CH2:21][C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)=[N:13][N:12]=2)=[CH:8][C:7]=1[OH:30]

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 6419393HCID 6419393, Verbindung

Produkt 1

HCID 22741987Vatalanib metabolite M26

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 2 ml boron tribromide (≈1M in CH2Cl2) is mixed with a suspension of 0.19 g (0.50 mmol) 1-(4-chloro-3-methoxyanilino)-4-(4-pyridylmethyl)phthalazine (Example 68B) in 4 ml dichioromethane at 0° C. under a nitrogen atmosphere. The resinous mixture is left to stand for 18 h at RT, the dichloromethane phase is then decanted, and the glutinous residue stirred with 10 ml THF and 5 ml sat. NaHCO3 solution. The resulting suspension is filtered, the filter residue washed with THF and discarded. The THF phase is separated and dried (Na2SO4), concentrated by evaporation, chromatographed (SiO2; acetate/CH3OH 40:1→19:1) and title compound crystallized from acetonitrile/methanol: m.p.: 245-246° C.; HPLC: tRet(Grads5-40)=8.8; FAB MS (M+H)+=363.

Aufarbeitung

  1. waitThe resinous mixture is left
  2. customthe dichloromethane phase is then decanted
  3. filtrationThe resulting suspension is filtered
  4. washthe filter residue washed with THF
  5. customThe THF phase is separated
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated by evaporation
  8. customchromatographed (SiO2; acetate/CH3OH 40:1→19:1) and title compound
  9. customcrystallized from acetonitrile/methanol

Quellen und Nachweise

ORD-Eintrag
ord-0396c00ac99b4d4f80b577a99a3e052b
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06258812B1

Notizen zur Reaktion

Wird geladen…